


Brotherly Love

by TammyRenH



Series: Masquerade fills [1]
Category: Supernatural
Genre: Bottom Dean Winchester, Don’t Try This At Home, M/M, Riding, Sex Toys, Unsafe Sex, mentions of switching, random switching of POV, rolling chairs aren’t good for sex
Language: English
Status: Completed
Published: 2020-04-14
Updated: 2020-04-14
Packaged: 2021-03-01 16:41:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,291
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23640226
Author URL: https://archiveofourown.org/users/TammyRenH/pseuds/TammyRenH
Summary: Written for the following masquerade prompt:  Sam loves it when Dean climbs into his lap and rides him.
Relationships: Dean Winchester/Sam Winchester
Series: Masquerade fills [1]
Series URL: https://archiveofourown.org/series/1701883
Comments: 8
Kudos: 121
Collections: SPN_Masquerade Spring 2020





	Brotherly Love

**Author's Note:**

> First of 4 masquerade fills I’ll be claiming this week. Also first time writing bottom Dean so fair warning

As far as sex went, Sam and Dean were very much open to just about anything. Since neither had been in a gay relationship before that drunken night in Maine so many years ago, they never had and never bothered defining roles for themselves – they both topped, they both liked to bottom, and both boys found themselves on their knees frequently and enthusiastically. Dean somehow managed to be both softer and bossier in the bedroom than Sam, Sam sometimes felt the need to pound his brother into the mattress (or against the wall, the table, the kitchen counter). But no matter how the sex went down, they both enjoyed it, enjoyed each other.   
  
They had been on a hunt, a vampire den in Montana, which meant late nights and long hours to track the nest, take the blood suckers down, and find and eliminate the ones that had gotten away in the melee. Too much caffeine, too little sleep, and jittery boys meant that the last thing that either one of them had thought about was sex.  
  
Going one or two days without sex was normal. Three or four during a hunt was not out of the ordinary. But between travel time and how long the hunt took, it had been eight days since Sam had fucked Dean against the bunker door before they left for Montana, which was a long dry spell for them. Not that either one of them was counting.  
  
But now they were back in the bunker. Sam had slept most of the way back home, Dean had grabbed five hours after they arrived which was more than enough for him. Sam looked up from his book as Dean walked into the library. He was wearing only a loose pair of sweatpants, his hair was adorably tousled, and his lips looked a little swollen like he had been biting them.  
  
And he was walking odd – nothing that anyone else would notice, but there was something off about the way he was moving.  
  
“Is it me or have you gotten more bow legged as you age?” Sam asked, putting down the book he was reading and twirling the chair around to face Dean. “I mean, at this rate by the time you’re ninety your legs will be so far apart from each other that if you climbed up on a horse your legs would never actually touch it.”  
  
“Fuck you.” Dean muttered, but there was no heat in his voice. However, a very interesting flush crept across his cheeks.   
  
Sam started to stand up, go to his brother, and kiss him until that blush covered Dean’s whole damn body, but Dean stopped him.  
  
“Lose the pants.” He ordered. “And then sit your ass right back down.”  
  
Sam’s cock was already twitching as he assimilated the words. Of all the many ways they had sex, this was one of his favorites, if not his very favorite. His jeans were feeling extremely uncomfortable and Sam was quick about getting out of them, tossing off his shirt for good measure. Dean stayed where he was, his hungry eyes tracking Sam’s movements.   
  
The chair Sam was sitting in used to be a computer chair, but somewhere along the way the arms had broken, and he had taken them off when he got tired of dealing with them. He liked the chair though, it was well worn, comfortable and he liked being able to wheel from one part of the table to the other, cause generally he had several books he was plowing through at once.   
  
Usually when they did this, it was on the bed with Sam on his back and Dean over him. They had never attempted this on other furniture before, much less a chair that rolled and since neither of them were small men, Sam was a bit worried about the chair taking their combined weights, especially with the bouncing and all (cause Dean was one champion bouncer), but as he sat down on the chair, his cock already semi-hard with anticipation, he couldn’t bring himself to care. If it broke, it broke, it would be worth it.

Dean still hadn’t taken off the sweatpants and Sam was more than ready to get this show on the road. “Did you bring lube?” He asked. They really needed to stash that shit everywhere, because apparently Dean had decided everywhere was fair game for sex and Sam was more than on board with that notion.  
  
Dean’s tongue crept out, Sam watched in rapt fascination as the tongue licked Dean’s lower lip, already a bit swollen and so full and so tempting and then Dean shook his head.  
  
Sam sighed and started to get up, but Dean growled. “I said stay where you are.”  
  
Well all right then. Sam sat back down and folded his arms around his chest. If Dean thought he could take Sam without lube, he could just try and see how far he got.   
  
Dean smirked at Sam and damn if that smirk didn’t do things to Sam’s insides, made him want to squirm on the chair.  
  
Then Dean pulled down his sweatpants, eyes on Sam the entire time, turned around and bent over, his tight perfect ass right in front of Sam.  
  
“Fuck, fuck – I can’t believe you, Jesus. Fuck, Dean.” Sam sputtered as he stared at the very large, very purple, plug in Dean’s ass. He could see the lube dripping from around Dean’s hole and Sam just – “Fuck.”  
  
“Exactly the wise and witty words I would expect a Stanford almost-grad to use.” Dean still had that damnable sexy smirk on his face as he looked back over his shoulder at Sam. He backed up, until they were almost touching and then batted those ridiculously long eye lashes at him, and his voice was so low and sexy that he was practically purring. “Do you want to do the honors?”  
  
Two could tease, and Sam took his hands, rubbed them over that perky ass of Dean’s before slowly reaching for the plug with one while the other gave a few well deserved slaps to Dean’s ass. Dean was already cursing before Sam began to slowly pull the plug out, only to slam in back in with perhaps a bit more force than he should have. Dean shouted, and probably would have tipped over if one of Sam’s hands hadn’t grabbed hold of a hip.   
  
Despite Dean’s threats to his manhood, Sam played with the plug for a few more moments, twisting it, pulling it back out watching as Dean’s hole gobbled it back up when he pushed it back in. Dean’s legs were shaky, and they were both hard when Sam finally pulled it all the way out and carelessly tossed it to the floor.  
  
Before Dean could say anything, much less move, Sam stuck two of his fingers in where they plug had left. Dean had used a lot of lube, his hole was sloppy wet, and Sam felt the lube squelch as he scissored his fingers in and out of his brother, he used his other hand to keep Dean where he wanted him.  
  
“Damn you Sam, if you don’t quit fucking around and get to fucking me, I swear I am going to bite off every fucking body part I can reach.”  
  
“Now who is the eloquent one?” Sam asked as he withdrew his fingers. Before Dean could respond to that, Sam turned Dean around, Dean would have fallen if Sam’s hands hadn’t kept him upright and then Sam lifted Dean up, causing a very undignified sound to come out of Dean that Sam fully intended to tease him about later. With just a bit of strain, Sam pulled him on his lap, letting the tip of his cock tease Dean’s sloppy entrance.  
  
They hadn’t used a condom for years, not since they had decided that they were all each other needed, and Sam couldn’t wait until his bare cock was buried deep into his brother. But for now, he held Dean in place right above his cock and then looked down at his brother, and he was the one smirking as Dean tried to wiggle out of his grasp.

“Let me down you fucking moron.” Dean snarked and Sam let go of him like the good brother he was. Dean found himself falling almost halfway down his brother’s very large cock.  
  
“Fuck!” Dean grabbed the back of the chair, his face very close to Sam’s and he decided the best fucking thing to do was to kiss that smirk right off of Sam, because if there was one thing Dean was better at Sam than, it was kissing. Plus it would give him a chance to get used to the burn of that huge fucking cock crammed inside him, but that was his secret. No way was he letting Sam know that every single time Sam topped he had to fight through the burn and the bright flare of pain before he could fully take Sam’s cock.  
  
Sam’s eyes darkened and then closed as Dean leaned in, and Dean felt rather than heard Sam’s sigh as his lips claimed Sam’s. There was nothing gentle about the kiss, this was about deep hunger and insatiable need and there was a clash of tongues, more than a little bite of teeth, and as Dean began to drown in the sensation, he found himself relaxing just enough to slide down a bit further on Sam’s cock.  
  
It was a long, torturous slide, their lips never parted. Dean held on to the back of the chair for all he was worth, he was determined to take this slow, make this last. Sam, the bastard, apparently didn’t feel the same way and those gigantic hands of his, those talented, twisted, exquisite gigantic hands of his, began playing with Dean’s nipples. Stroking and teasing and then there were twin bursts of pleasure-pain as they were both pinched and Dean broke away from the kiss with a gasp and then slid the rest of the way down, landing hard on Sam’s lap.  
  
For a moment they both just breathed heavily, staring at each other’s red and swollen lips as Dean tried to ride the wave of pain-full-pain that was always a part of taking Sam’s cock. It was the way Sam’s cock filled him inside, the way it pushed so beautifully brutally on his prostate, the way it made him feel so connected to Sam, that helped him deal with the pain and kept him coming back for more.  
  
Sam was still playing with his nipples, the fucker, and now they were as red and swollen as his lips and the need to move was overwhelming. Dean’s feet were planted firmly on the ground, and he pushed up, only about halfway off of Sam’s cock, and then let himself slide back down again.  
  
“Fuck.” They said in unison and then grinned at each other. Dean repeated the motion, the chair was moving slightly on its wheels every time he slid back down. Sam was using his legs to try to brace the chair, but it was a bit like having sex on a rocking chair must be and Dean filed that thought as a maybe to try someday.  
  
“You take my cock so beautifully.” Sam murmured, hands thankfully no longer torturing his nipples, but sliding up and down Dean’s side, not guiding him, not yet, but they both knew it was a matter of time before Sam took control and Dean shivered with the anticipation of it. “It’s so big inside of you, fills you up to the brim. Isn’t that right big brother? I just fucking love the way your ass is so tight around my dick, squeezes it so good.”  
  
Dean would have come back with something both witty and sexy, but he was too busy being lost in how damn fucking great it felt every time he pushed part way off of Sam and slid right down again. The pain was fading away into a dizzying pleasure, like it always did, and although Sam’s cock wasn’t hitting his prostate dead on, it was nudging it enough that Dean’s cock, which had flagged during the initial penetration, was hard and hungry for more.  
  
“Come on sweetheart. Ride it like I know you can.” Sam murmured, lips on his neck, teeth teasing a line against his shoulder. “Practically a pro at this now, aren’t you Dean?”

Sam and his fucking dirty talk and his fucking dirty mouth and Dean leaned over to claim it once more, and the next time he pushed off, he pushed all the way off and then slammed himself back down, all the way down, ignoring the flare of too much, too full. He smirked satisfied at Sam who jerked in surprise, scooting the chair several inches. Dean was knocked off kilter, floundering and fighting the panic of falling, the tug on his hole border-lining on painful.  
  
It was Sam who set him back upright, pushed him down until he was fully seated on Sam’s dick and then held him there.  
  
“Sex on moving objects maybe not such a good idea.” Sam was breathing heavily..  
  
“Wimping out on me Sammy?” Dean asked, eyebrows raised and pretending that he was staying right where Sam put him because he wanted to and not because Sam’s grasp was so tight that there was no way he could fucking move.  
  
Sam’s grin was feral. He pushed the chair back with those long legs of his, until it hit the back of the table. Then his hands tightened on Dean’s hips, and Dean could just imagine the fingertip bruises that he would be wearing for days, and then he lifted Dean up as if Dean was a rag doll and slammed him back down on his cock.  
  
“Fuck, don’t fucking stop.” The chair was still moving dangerously erratically as Sam lifted him back up and back down again a few more times. When Dean was dizzy with the pleasure of being fucked so thoroughly, Sam let him go and taunted. “Now it’s your turn Dean, show me what you’ve got. That is, if you have anything left.”  
  
Maybe taunting Dean wasn’t the best idea, because Dean got that glint in his eyes, and then he tightened his legs against the chair, leaned over and nipped Sam’s lower lip. “Hold on tight baby brother.”  
  
Dean was riding Sam for all he was worth, so quickly up and down Sam had no time to adjust, then he did that swirly thing with his hips that always had Sam’s eyes rolling back in his head and he kept the rhythm, up and down and swirl and up and all Sam could do was hold on to Dean’s hips and feel the chair shake, feel his whole body shake, every time Dean pummeled down.  
  
Still, this wasn’t Sam’s first rodeo so to speak and he knew how to push Dean’s buttons. As Dean bounced, Sam leaned over and blew at Dean’s red and swollen nipples, causing Dean to curse and his rhythm to falter. Sam used that hesitation to begin thrusting up, ignoring how the chair was erratically shaking back and forth. He was too lost in how glorious it was to thrust into that heat, how eager Dean was to meet him, how angry and red Dean’s untouched cock was. He knew Dean wanted him to start stroking it without having to ask Sam, but considering the way that Dean had made Sam beg a few weeks ago –   
  
Their fucking was loud, what with the lube squelching and the moaning and the cursing and the way their bodies were slip-slapping together, so it was understandable that neither one heard the table groaning with the weight of the chair ramming against it.  
  
Sam was close, so close, and he could feel his balls begin to tighten, could feel how his brother was shaking apart on top of him, and he just needed a little more, and he grabbed onto Dean’s hips, started thrusting up erratically.

Fuck, he was close, he was so close, and if he could let go of the back of the chair long enough to touch his cock, it wouldn’t take much, just a stroke or two and Dean could feel how shaky his legs were, his fingers were aching because of how tightly they had held to the back of the chair and Sam was practically lifting them both up, shoving so fast and hard into Dean and fuck the chair was moving again.  
  
Sam cried out below him, he had lifted his hips halfway off the chair, buried his cock so deep inside of Dean that Dean could swear he could feel him in the back of his throat and fuck, there was nothing like this, nothing like being taken apart this way. He watched his brother’s eyes close as he climaxed, felt Sam’s hands tighten so painfully, so desperately on his hips and then Sam was filling him up deep inside and he was so hard - so close –   
  
The library table was wood and heavy and had stayed in the same exact place for decades but apparently could not withstand that force of Sam’s orgasm. The table skidded, causing the chair to start to fall backwards, and Dean didn’t have time to think much less react before Sam was standing, still buried deep inside of him and Dean’s body shuddered with the force of how that movement shoved Sam’s cock impossibly deeper into him. Dean was spilling between them, his untouched cock spurting and twitching in a release so intense he almost whited out. His orgasm seemed to go on forever, and he felt himself rock against Sam’s body, feel the mess of come between them.  
  
“Fuck, you weigh a ton. I can’t –“ and Sam sat right down on the floor, his cock slipping out of Dean’s hole as he did so. Dean tried not to notice how empty he felt at the loss.  
  
For a moment, they sat there, Dean’s body scrawled carelessly over Sam’s before Sam began to chuckle. “I really rocked your world, there didn’t I?”  
  
“I think you have it backwards.” Dean grumbled, wondering how long it was going to take before he could risk trying to stand. He was still pretty shaken up, and it wasn’t just because of the chair falling.   
  
“I’m not the one that came untouched, not to mention I fucked you so good you didn’t even notice you were about to fall. If I hadn’t saved us, your ass would have landed on the floor, some hunter’s reflexes you’ve got going there.” Sam teased, but his hands were in Dean’s hair, and his lips were smooth against Dean’s neck and Dean decided kissing Sam until neither one of them could breathe or think was a very appropriate response.  
  
Eventually the stickiness was too much to stand, they were both covered with Dean’s come, not to mention the come still dribbling from his ass and Sam stood up with a groan and held his hand out for Dean. It wasn’t unmanly at all the way that Dean took it and let Sam propel him back up.  
  
He swatted at Sam’s ass and grinned as Sam turned back to him and huffed. “Before you get too cocky, just remember – it’s my turn next.” He warned and pushed past Sam in a totally not trying to beat Sam to the shower way.  
  
As he was letting the water rush over him, and making room for Sam’s gigantic body to join him under the spray, he wondered where else they could try fucking, maybe the map table could take their combined weight…


End file.
